Pros and Cons of Upwork: An Analysis from a $600k Freelancer

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As someone who has earned over $600,000 on the Upwork freelance platform, I’m often asked about the pros and cons of Upwork.

Read Also: Can you make good money on Upwork? How I made $600,000 in 4 years

Upwork, for the uninitiated, is the world’s largest, and most popular freelance marketplace. 

On the site, freelance professionals can browse jobs posted by prospective clients from all over the world. 

Clients love Upwork because it allows them to shop for the best talent outside of their immediate area, in any niche imaginable. Plus, the Upwork hiring process is fairly straightforward.

Freelancers love it because it takes the dreaded “cold-pitch” out of the equation. Upwork clients are already ready and willing to hire. It’s a bit like fishing in a pond where you know the fish are biting.

The site’s most well-known competitors, who you may already be familiar with, include freelancer platforms and job sites like, Fiverr and Thumbtack.

However, Upwork is far from perfect.

And just like anything else, there are pros and cons. 

If you’re wondering whether or not those pros outweigh the cons, you’re in luck. 

Below, I have compiled a list of Upwork’s biggest pros and cons to help you decide whether or not Upwork is worth the hassle.

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Upwork Pros:

1. It’s easy to find freelance jobs and potential clients

Every new freelancer has asked themselves the same question at some point or another: Where do I find new clients?

Cold calls and cold emails require a ton of time with little payoff.

The same can be said for social media. 

And it’s next to impossible for beginners to score word-of-mouth referrals when your freelance work history is limited.

By contrast, finding jobs specifically catered to your specific expertise or skillset on Upwork, in most cases, is a breeze. Especially for the following popular freelance fields:

  • Graphic design
  • Machine learning
  • Data Analytics
  • Mobile development
  • Video production
  • Search engine optimization (SEO)
  • Web development
  • Writing

New clients are joining the platform on a daily basis. And dozens of new jobs are posted to the site every minute of every day by clients who are ready to hire.

You don’t have to convince them that they need the service. You don’t have to convince them of the benefits of hiring an independent contractor. They already know they need a professional, with a specific skill set, who can do the job.

You just have to convince them that you are the best candidate for that particular project or job posting.

And while that may sound easier said than done, with a bit of practice and preparation, sending winning proposals and landing jobs can be a breeze.

Read Also: How to write an Upwork proposal: 11 proven tips with samples

2. Upwork handles the contract, billing, invoicing and mediation

Another problem that frequently plagues the freelance community is the subject of how to handle contracts, billing, invoicing and mediation (in the unfortunate event something goes wrong). 

These tasks can be especially daunting for new freelancers. And expensive.

Using myself as an example, when I am not freelancing on the Upwork platform, I pay Fiverr Workspace $216 per year to handle my invoicing and payments. And I incur fees from payment processors like PayPal and Stripe.

Not to mention the fact that there’s still a lot of manual work involved even with the help of these platforms. 

Read Also: Best tools for freelancers: 14 essential resources for your business

And heaven forbid there’s ever a payment or contract dispute. I’d have to file my own claims and hire my own legal counsel. 

It can be a scary world out there when you are on your own.

This is why, in my mind, one of Upwork’s greatest “pros” is the often looked-over fact that they handle all of those backend operations for you.

Your Upwork proposals (as well as messages sent through the Upwork messenger) essentially serve as your contract.

Upwork also helps handle payment collection, bank deposits and even your 1099 (if applicable). 

And should a dispute with your client arise, Upwork customer service is ready to help. They can reach out to the client on your behalf, and even assign a mediation agent if no agreement can be reached.

3. You can make a ton of money on the platform

And of course, the greatest pro is that you can make a lot of money on the Upwork platform. 

As a graphic designer, I personally pull in over $100,000 per year on Upwork at an hourly rate of $150.

And I’m not alone.

Freelancer Josh Burns, a SQL Server DBA, has earned over $800,000 on the platform.  

I will openly admit, that it can be hard to land those first couple of gigs on Upwork. It took me almost two weeks to get my first job offer after consistently applying nearly every day.

And it can take weeks to build a good reputation on the platform.

But after a while, you start to get a feel for exactly what to say and how to pitch yourself to prospective clients. At least I did.

Read Also: How I got my first job on Upwork: Advice from a $600k freelancer

Today, I mostly keep my Upwork profile set to “unavailable” because I stay so busy I don’t have time for new clients.

Speaking of which, I’ve also used Upwork to hire subcontractors as well. Delegation and hiring out for some of the more monotonous tasks have significantly improved my bottom line, helping me make even more money along the way.

It all sounds great so far, right? 

Well, buckle up because now we get to the “cons” portion of the article. 


Upwork Cons:

1. You have to pay to play

In prior years, freelancers could bid on as many jobs as they wanted for free.

But this caused issues for the online platform. 

Namely, jobs were being flooded with too many, often underqualified, candidates. 

Believe it or not, many Upwork freelancers indiscriminately apply for jobs without reading the job post or taking the time to consider whether or not the job is even right for them. 

This, as you might imagine, was frustrating for many reasons.

The main problem was that it made the clients’ selection process (and ability to find the right freelancer) needlessly more time-consuming due to the overwhelming number of freelancers flooding the talent pool.

And so, in May 2019, Upwork introduced something called “Connects”. 

Upwork Connects essentially acts as a digital internal currency or credit.

Today, freelancers have to spend 2-16 Connects for each proposal they send (depending on the size of the job). 

This encourages freelancers to be a bit more discerning when it comes to sending proposals.

While Upwork gives all new users 40 free Connects to start, most new Upworkers tend to blow through that first allotment pretty quickly and will end up purchasing more.

Now, there is some good news here – you don’t have to spend any Connects to apply for jobs to which you were invited. And most senior freelancers on the platform end up (mostly) only replying to invites over time and ignore the job feed altogether. 

And the longer you’re on the platform, the more invites you’ll start to receive. I personally haven’t used or purchased any Connects in years.

Plus, you receive free Connects every time you win an interview. The more interviews you win, the more Connects you begin to rack up.

In summary, the bulk of this expense will occur during your early days on the platform … when you aren’t winning interviews as often and aren’t receiving invitations to apply.

It’s one of those things that gets easier with time.

Editor’s Note: There are additional fees you may also encounter while using the platform like boosted proposals and boosted availability badges. However, it is entirely possible to win jobs without paying for these items.

2. You have to pay Upwork’s commission fee

Next, let’s address the most common complaint about the platform – Upwork’s fees.

At the end of the day, Upwork is still a business. They have business expenses, employees to pay and investors to make happy.

They have to make money.

And the bulk of that money is made through their service fee – a flat 10% on all contracts. 

Lastly, I offer this food for thought … one has to keep in mind that Upwork is not entirely different from a recruiting agency. And the average agency fee is closer to 30% across the board, regardless of earnings.

By comparison, 10% seems like a deal.

Read Also: 3 Ways to Avoid Upwork Fees from a $600k Freelancer [2023]

Editor’s Note: Upwork used to charge a sliding scale fee based on your billings with each unique non-Enterprise client (5% to 10% to 20%). They switched to the flat 10% fee in May 2023.

3. You have to keep your clients on the platform for two years

Want to get out of paying that Upwork fee altogether? No problem, after a couple of years you’re allowed to take your long-term relationships off the platform and work with them directly. 

However, taking your client off-platform early without paying the conversion fee (roughly 12% of the freelancer’s estimated annual earnings on Upwork) can result in a permanent suspension of your Upwork account. 

While this may seem unfair, I always advise not to bite the hand that feeds. Two years will come and go before you know it.

There you have it, the three biggest pros and cons about the Upwork platform – at least in my opinion. 

For me, the cons have never outweighed the pros.

Upwork gave me the lift I needed to break free from a job I rage-quit back in 2017 and turn my then side hustle into a full-time freelance career.

Sure, it was hard to get started, secure that first client and rack up that initial set of positive reviews for my profile. Sure, I’ve paid a lot of fees to the platform. But it’s also been an amazing tool in my freelance toolbox that I wouldn’t exchange for the world.

What do you think? Do the pros outweigh the cons? What do you think is the worst thing about the Upwork platform? What do you think is the best platform for freelancers? Let me know in the comments below. And don’t forget to connect with me on social media – I’d love to hear from you!

PS: If you’ve found this article helpful, and you feel so inclined – buy me a coffee (leave a tip) on Kofi!

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Morgan Overholt

Morgan has almost 20 years of professional experience in graphic design and a bachelor’s degree in Computer Science. Her successful freelance business has been featured in articles that have appeared on, Refinery29 and Business Insider Prime.

6 thoughts on “Pros and Cons of Upwork: An Analysis from a $600k Freelancer”

  1. What always slightly annoys me about Upwork is that while yes, it’s nice that they handle contracts, billing, etc — use of the platform comes with a whole extra set of Upwork-specific mental overhead that you need to think about (what will this action do to my JSS? how should I budget my connects?). And the skills and knowledge you acquire over time to deal with these things are obviously very platform-specific, and often not intuitive to new users. So users end up locking themselves into the Upwork platform, when they’d be better served by using multiple channels.

    (Obviously that’s fine if you’re happy working on Upwork exclusively, but I always advise people to diversify! Avoid single points of failure, etc.)

    Perhaps one for your cons column? 🙂

  2. Oh! I love this one! It’s so very true. Even at my level, I tend to stress out about hounding my clients for positive feedback at the end of an engagement. The pressure to maintain a perfect record on Upwork is unreal!

  3. Morgan, I love your content! Expert yet straightforward advice that is giving me renewed hope for Upwork. I have been on the platform now about a year and a half and it has been a wild ride. I have dealt with such a parade of personalities, from flakes to con artist to abusers. Through sheer persistence I have managed to gain top rated status and I’m now focused on winning better quality jobs and clients. Despite having nearly 20 years of experience as a freelance writer, my inexperience on the platform (and failure to educate myself thoroughly about it) has resulted in a loss of well over $1000 to clients who defaulted on payment. Knowledge is power! I wish I would’ve had your jumpstart kit from the beginning. But thank you for publishing all of this great advice. One thing I’d love to see you write about is a breakdown of the Upwork terms of service, so that we as freelancers can better understand what we are getting into and how to protect ourselves. Thanks again!

  4. Oh wow, Michele – I am so sorry to hear about those awful clients.

    I certainly had a couple in the beginning too. I was much more “flight” than “fight” whenever I found myself in a potentially bad situation.

    I learned early on that if no money was exchanged, the client couldn’t leave me a bad review – or any review for that matter. This is why on two occasions (that I can remember) I saw the warning signs and cut the contract before money ever changed hands.

    I also switched to hourly (protected) billing after a couple of bad eggs decided not to pay me the previously agreed upon fixed rates. It is my hope that others learn from both my mistakes AND my wins to better protect themselves from day 1!

  5. Thank you for the tips and cheat codes. I’m definitely new to freelancing but I’ve heard about it mentioned elsewhere. I landed my first gig in a couple minutes. Lets just cross our fingers I get paid. A bit skeptical. Yet hey your advice will help thank you for your knowledge, the pleasure is mine.

  6. Thank you for the advice the pleasure is mine. Was able to land a gig in a coupe of minutes. Superb.

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